Author:
Forsyth Craig M.,Francis Craig L.,Jahangiri Saba,Liepa Andris J.,Perkins Michael V.,Young Anna P.
Abstract
N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 reacted with pyrazol-3-ones 2 under a variety of conditions to give pyrazolo[2,3-e][1,2,3,5]oxathiadiazine dioxides 3 and pyrazolo[3,2-b][1,4,3,5]oxathiadiazine dioxides 5, and frequently, one or both of pyrazolo[1,2-b][1,2,3,5]thiatriazole 1,1,5-trioxides 4 and 1,1,7-trioxides 6. In all reactions, the pyrazolo[3,2-b][1,4,3,5]oxathiadiazine 5 was the major product, with the pyrazolo[2,3-e][1,2,3,5]oxathiadiazine 3 being a significant product in the absence of base. Prior to our recent work, the core ring systems of compounds 3 and 5 had not been reported and compounds 4 and 6 are new derivatives of a rare ring system.
Cited by
10 articles.
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1. Bicyclic 5-6 Systems With One Bridgehead Nitrogen Atom: Four Extra Heteroatoms 3:1 and 1:3;Comprehensive Heterocyclic Chemistry IV;2022
2. 1,2,3,5-Thiatriazoles;Comprehensive Heterocyclic Chemistry IV;2022
3. N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIV. Synthesis and Reactivity of the New Benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine Ring System;Australian Journal of Chemistry;2018
4. New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines;Arkivoc;2016-06-06
5. Heterocyclization of N-(chlorosulfonyl)imidoyl chlorides with anilines, a new method of synthesis of 1,2,4-benzothiadiazine 1,1-dioxides;Chemistry of Heterocyclic Compounds;2016-04